


Better Selves

by OneWhoSitsWithTurtles



Category: Critical Role (Web Series)
Genre: Alternate Universe - Canon Divergence, Anal Fingering, Anal Sex, Barebacking, Blow Jobs, First Kiss, First Time, Friends to Lovers, Friendship, Kissing, Love Confessions, M/M, Neck Kissing, Second Chances, Spoilers, Virgin!Essek
Language: English
Status: Completed
Published: 2020-03-25
Updated: 2020-03-25
Packaged: 2021-02-28 23:21:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,517
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23315299
Author URL: https://archiveofourown.org/users/OneWhoSitsWithTurtles/pseuds/OneWhoSitsWithTurtles
Summary: MAJOR SPOILERS FOR C2E97 - 99.Floating on the high seas, Caleb cannot bear to see Essek leave his sight again without first confessing his feelings. Caleb can only hope that Essek may return those feelings, and that the Mighty Nein won't forsake him for the emotions he can no longer ignore.
Relationships: Essek Thelyss/Caleb Widogast
Comments: 17
Kudos: 312





	Better Selves

**Author's Note:**

> A/N: This was how I wished episode 99 ended :3 And now that CR is on hiatus, even though I'm glad the cast is being safe, I couldn't resist indulging. This is my first time writing in months, and my first time ever writing this pairing, so here we go! I hope you enjoy ^.^

The Mighty Nein stood in a loose circle on the deck of the _Ball Eater_ , watching the armadas of the Empire and the Dynasty slowly part ways. Caleb stood tense with bated breath, awaiting a betrayal that never came. No cannons were aimed; no ship shifted out of line. Shockingly, their move at peace had been a success. Caleb could still hardly believe it as he kept a hand on Beau's shoulder to stay steady while everything sank in.

Caleb remained lost in thought as the rest of his group began to hesitantly speak and celebrate the victory. He only clicked back into the present moment when Essek began to speak. It wasn't Essek's voice or words that caught his attention but instead it was Essek's eyes, seeking Caleb's gaze twice as often as anyone else in the group. Essek had been quiet throughout the majority of negotiations, hovering close but nervously. Caleb understood Essek; the desire to be close to friends during tense times warring with a fear of rejection after the Mighty Nein learned of his involvement with the war.

Fjord was the one to ask the question they all wanted answered. "Where will you go now?"

Caleb fixed his gaze on Essek's disguised face as he listened to the response. Even when Beau took a threatening step towards Essek, asking what 'loose ends' he intended to kill, Caleb dropped his hand from Beau's shoulder but did not look away. He realized then that his group's trust in Essek had been shaken even deeper than his own, perhaps because they hadn't committed unforgivable acts the way Caleb and Essek had. But Caleb saw the weight in Essek's eyes, acknowledging what he had done and what it could cost him if his friends deemed him unworthy of a second chance. Caleb understood that fear because it was also his own every time the Mighty Nein learned a sliver more about his past and the atrocities he had committed.

Essek and Beau were now staring at one another, the air tense with distrust. In an attempt to diffuse the moment, Caleb spoke up. "Well, we have our peace so... happy days."

Essek's eyes snapped to Caleb the instant he spoke, and remained there as he chuckled. "Happy days," Essek echoed, his softening gaze lingering. There was a pregnant pause and then Essek lifted his hands, beginning the movements for his spell to return home. "Until then."

Caleb held back, telling himself that now wasn't the time and there would be another chance to speak later. However, despite the tension in the air, peace had just been achieved between two warring nations and Caleb sought to continue that theme of truce. "Wait!" He stepped forward and wrapped a hand around Essek's forearm. "I need to speak with you."

He had been ready if Essek finished the incantation and teleported them both but Essek's movements broke off, nullifying the spell before its completion. Essek's reaction had been so quick that Caleb almost wondered if Essek had hoped for Caleb to reach out for him. The thought had Caleb's stomach squirming with nerves, which burst into a hive of maddened butterflies in his chest when Essek stared at him openly. "Anything you need, Caleb."

"Fjord, may we use the captain's quarters for a brief private conversation?" Caleb requested, trying to be respectful and probably sounding awkwardly formal.

It didn't help that Jester was smirking and elbowing Fjord in the ribs as she repeated in sing-song, " _Private conversation_."

Fjord, to his credit, tried to keep a straight face as he nodded. "Have at it."

Caleb barely made it two steps before Beau's iron grip locked on his wrist, and Caleb resisted the urge to tighten the hold of his other hand on Essek's forearm. "What the hell are you doing?" Beau whispered, which wasn't much of a whisper at all. Her expression was equal parts curious and distrustful. The distrust hurt, but Caleb hoped that with time and the proper actions, they could get back to that moment when Veth had welcomed Essek to the Mighty Nein – and this time, mean it.

Caleb did not shy away from her gaze. "Trust me. Please."

Beau pursed her lips, thinking for a long moment before suddenly letting go. "Be careful," she muttered and stepping out of his path.

Caleb looked around the group but no one else spoke up or moved to stop him. Caleb then looked at Essek, who was watching him closely. Caleb slid his hand down Essek's forearm to instead take his hand, another flutter of nerves overtaking him when Essek followed willingly in the direction of the captain's quarters. Once they were inside the large room, Caleb dropped Essek's hand and focused on muttering a spell to close the door and windows' drapes.

Only then did Caleb let himself look back to Essek, and he swallowed. "I want to see you, not this illusion."

With a single word and a small hand movement, the disguise of Dezran Thain melted away and Essek was before him, feet planted firmly on the wood floors. Since he had been in disguise, Essek had not worn his full mantle and robes and was instead dressed in a comfortable but stylish tunic. Caleb let his eyes wander even as he stepped back into Essek's personal space, taking in his warm eyes and beautiful dark skin. When Essek wasn't floating they were nearly the same height, Essek tilting his chin upward a bare inch.

Essek allowed Caleb to stay in his personal space and walk him backwards until his back was pinned to the room's door. "Here I am," Essek's voice was hushed.

"Here we are," Caleb answered, just as softly.

There were so many things Caleb wanted to say and ask, but there was one thing he needed to know before anything else. He held his body flush against Essek, their legs tangled together and Caleb's hands gripping Essek's biceps. Caleb waited and watched Essek, noting every detail. Caleb knew what he wanted but he needed to know if Essek truly wanted it as well. He got his answer when Essek's gaze tracked down Caleb's face to linger on his lips, Essek's cheeks darkening with a flush of obvious desire.

"I meant what I said when you all confronted me," Essek told him quietly, eyes still on Caleb's mouth. "I had never cared for anyone but myself for over a century. I never planned for any of you, but _especially_ not you."

Caleb slid his hands up from Essek's arms, over his shoulders and clavicles before traversing the column of his neck. Essek leaned into the touch and breathed in sharply when Caleb's fingers caressed the shell of his pointed ears. And then Caleb dug his fingers into Essek's hair and pulled him firmly into a kiss, knowing that no other words were needed between them in this moment. There was no fight from Essek as he melted into the kiss and looped his arms loosely around Caleb's waist, holding them even closer together.

Caleb had never been more elated or terrified in his life so he took his time, memorizing the shape and weight of Essek's lips against his own. Caleb kept one hand in Essek's soft hair but moved his other hand down to cradle Essek's cheek, feeling how warm and alive he was. He had wanted Essek for a long time, even if he had ignored that desire for nearly as long, and it felt blissful to finally have Essek in his arms.

With a tilt of his head, Caleb deepened the kiss. Essek moaned into his mouth and pressed more eagerly into the kiss, causing their hips to align. Fire sparked to life in Caleb's gut and he broke away with a groan. They were both breathing heavily even though they had done nothing but kiss. There was a lot more Caleb wanted to do with Essek but now wasn't the time; he had no doubt that his group was hovering nearby and being as nosy as possible.

Essek glanced over to the curtain-drawn windows and then withdrew his arms from around Caleb, his expression pensive. "I will not let you risk a wedge in your group over me."

"Now is not the time to be self-sacrificing." Caleb huffed a laugh but he trailed off when Essek turned sombre. "Essek, listen to me," Caleb implored. "Those people out there are my family—"

"And they do not trust me," Essek cut him off.

"Nor should they," Caleb shot back.

"I do not disagree," Essek said quickly. "But I will not let you risk—"

" _Let me_ ," Caleb scoffed. "I will never again _let_ someone control what I do. Now will you please just _listen_?"

Essek's lips thinned into a narrow line but he said nothing else to interrupt.

Caleb took a deep, steadying breath, and tried to get his thoughts in order. "I meant it when I said the differences between us are razor thin. I thought my intentions were important too, and it cost me my family. I never thought I'd find family again but then I met that motley crew out there and I was proven wrong. And I will not lose my family a second time."

Essek opened his mouth to speak but held himself back. Instead he rested a hand on Caleb's shoulder, giving him what he needed in this moment. Encouraged, Caleb continued. "That's why I needed to talk to you today. I know it's not right to ask someone to change for you, yet I stand here pleading again for you to find your better self. That regret you feel – that weight on your shoulders is _my_ regret, _my_ weight. I know it well." Caleb paused to place his hand atop Essek's, taking comfort in Essek's movement to lace their fingers.

"I'm not saying if they're right or wrong but it terrifies me to hear the group talk about seeking justice against you because we are the same," Caleb confessed. "Many days I wake up knowing I do not deserve them and certain someday they will realize that. I am damned for what I did and no spell can undo what either of us has done. But even if I cannot be redeemed I choose to fix what I can and I want you to join me in that endeavour."

When Caleb finished speaking he felt wiped out, spent. Essek tilted his hand and moved it to cup the curve of Caleb's neck, his thumb stroking the delicate hollow of Caleb's throat. "I value your faith in me, but I fear my actions are too damning for the others."

"Trust comes slowly for the group; slower still after a betrayal," Caleb acknowledged. "If it is not a challenge you wish to take on I will let you leave and never expect anything from you again."

Essek took the single step away from the door necessarily to be back in Caleb's personal space and Caleb's arms wound instinctively around Essek's waist. "If you are willing to take the risk despite your family's concerns, I will do everything in my power to be worthy of the chance you are offering."

All Caleb could do was nod his confirmation before Essek used his hand on Caleb's neck to reel him back into another kiss. Caleb immediately pinned Essek back against the door with his body, sparing only the briefest thought to how Jester or the others may react to the _thump_ sound against the door if they were eavesdropping. Then he stopped caring and focused on kissing Essek breathless. Essek was eager to reciprocate, one hand holding the back of Caleb's neck and the other roaming freely over Caleb's chest and hip.

Caleb parted his lips and Essek followed his lead, moaning softly when Caleb's tongue entered his mouth and explored. It didn't take long for Caleb to realize that Essek's movements, while willing, were hesitant and awkward. He wondered if Essek had ever shared this with anyone before, and that thought forced Caleb to pause and break the kiss a second time. Essek cursed under his breath and levelled Caleb with a stare. "Are you trying to torture me?"

"Essek, have you done this with anyone before?" Caleb asked gently.

Essek's flushed face darkened further as he looked away quickly. "If I am not pleasing you—"

"That is _not_ the concern," Caleb assured him, punctuating his statement with a slow thrust of his hips. It was easy to feel each other's interest through their pants.

Essek weathered his bottom lip and glanced back shyly. "I truly never cared for anyone else before you."

"Then I will not rush your first time," Caleb stated firmly, unwilling to entertain any argument. "Understand: I am not ashamed of this, nor do I fear what they may say. But I do not share well and I plan to take my time with you."

He felt, and was pleased by the tiny shiver that worked up Essek's spine upon hearing those words. "I understand," Essek said, and Caleb could see in his face that it was true. "But soon?"

"Tonight?" Caleb suggested. "No one sleeps in here and the sheets have been changed since the attack on Fjord. You could wake me with Sending when you arrive and I will come here."

"Alright; tonight," Essek agreed. A small, coy smile was curling Essek's lips as he leaned in to steal one chaste kiss before he waved his hands, muttered a few words, and vanished.

Something ached deep in Caleb's chest when Essek was out of his sight but he knew it was for the best, at least for now. He remained in the room alone for a few minutes, fanning his face with a hand until the flush of arousal abated from his body and skin. As Caleb had expected, every member of the Mighty Nein was still on deck when he stepped out of the room, though only Jester stood close enough to be unabashedly guilty of eavesdropping.

Jester's tail twitched with excitement behind her but Caleb saw that her expression was melancholy as he approached. "How much did you hear?" he wondered, unable to be angry at her for her curious nature.

"I moved away when you fell against the door." Jester giggled but sobered quickly. "Caleb, I'm sorry what we said about punishing Essek scared you. I'm still learning that the world is a lot greyer than the books I read growing up." She hugged herself and sighed, considering him for a long moment. "I can tell Essek really cares about you, and that you care about him too. We just want you to be safe but I trust you Caleb, _I do_. So I'll trust your judgement about Essek too."

"Thank you, Jester."

He accepted her hug when Jester sought it, affectionately wrapping an arm around her until she was satisfied and pulled away. "Veth and Beau will probably take the longest to come around, but I think they just need to see that Essek's intentions are good now, not just important."

Caleb gave her a smile. "I hope after Traveler Con we will get that chance."

#

Caleb knew the rest of the group was just as curious so he brought them all together for a group discussion while they sailed in the direction of Rumblecusp. Without sharing all the personal details, Caleb did his best to express to the group what he had told Essek; the ongoing weight of his guilt, his kinship with Essek's pain, and the fear he felt at the thought of the Mighty Nein turning on him the way the group spoke about punishing Essek.

Caduceus and Yasha warned him gently to be careful but were otherwise supportive and encouraging. Caleb had expected as much; Caduceus always tried to see the potential best in everyone and Yasha was familiar with the weight of past demons. Jester had already said her piece to Caleb directly but repeated it for the group to consider. Fjord seemed apprehensive but mollified by the judgements of Caleb, Jester, Caduceus and Yasha.

Veth and Beau were the most resistant, as Jester had predicted. Veth was concerned about Essek's intentions and protective of Caleb's wellbeing. Caleb implored her to give him a chance, and to consider her own words from over a week ago when she pointed out that Essek wasn't terribly different from the other members of the Mighty Nein. In the end they came to an agreement that Veth would give Essek a chance but if he hurt Caleb, Veth would shoot a crossbow bolt through his eye. It wasn't ideal but Caleb accepted what he could get.

Beau's arms were crossed when Caleb at last turned his attention towards her. "He's a _war criminal_ , Caleb. You want me to just sweep that under the rug because you have the hots for him?"

Caleb blushed but was undeterred. "I'm not denying what he has done. I am only saying that it is not that simple. I am sorry to bring this up but what about Yasha's actions in the eyes of those affected?" He noticed Yasha grimace but also saw her give a tiny nod; she understood the weight Caleb carried, to some extent at least.

"Yasha didn't have control," Beau snapped.

"Does that make it any easier for the loved ones of those she killed?" Caleb asked.

"It's different," Beau stated through clenched teeth.

"Says who? You?" Caleb raised an eyebrow. "Are you to be the world's judge on what is just and unjust? If so, tell me: how is what I did to my family and others okay? I followed Trent willingly for a long time before I became unwilling. What about all of the people whose loved ones never return home because we cut them down in battle?"

Beau's hands were clenched into fists at her sides. "Fuck you," she whispered, barely heard over the ocean's breeze.

"Beauregard, _none of this_ is simple. That's the point," Caleb sighed. "All we can do is find people who want to do good and are worth caring about, and try our best. And I... I really care about Essek. So all I'm asking is that you give him a chance to atone and try to do good."

Beau stood for a long moment, staring Caleb down while the rest of the group waited with bated breath. When she moved it was at the speed of lightning, punching Caleb's upper arm hard enough to make his eyes tear up. Caleb bit his tongue and took the hit. "He better prove that he's in it for more than just a good fuck," she huffed and then stormed away below deck. Caleb cringed with embarrassment but it was the best he could hope for. All he could do now was let everyone digest what he had shared with them and ruminate on what lay before them. Essek would have to prove himself to the group but that could only come with time and actions.

"Want me to heal that for you?" Caduceus offered, dropping a hand on the shoulder above Caleb's throbbing arm.

Caleb grimaced. "No, I deserve it."

"You don't deserve all the pain you are capable of finding for yourself," Caduceus told him. "But I respect your choice."

Caleb nodded his thanks and turned to Yasha. "I'm sorry about reopening old wounds for the sake of philosophical argument."

"The wounds were still open," Yasha answered. "And your argument was not wrong."

Everyone parted ways then, taking over their various roles to keep the ship sailing smoothly until the night crew took over. Beau did not join them for dinner but she did join them in their new bed chambers a few minutes before Caleb summoned the dome. Their eyes met and after a moment Beau gave a half-hearted shrug. Caleb would not push for more from her then; he was just happy to have everyone bedding down together beneath the safety of the dome.

#

_Caleb_.

Caleb sat up quickly, instantly awake. He had meant to stay awake until Essek sent him a message but must have drifted off as the evening edged towards midnight. Caleb rubbed sleep from his eyes and looked around the room. His heart seized with panic when he saw that Caduceus was sitting up in bed and looking at him knowingly. Caleb opened his mouth to say something but Caduceus shook his head and motioned for the door.

"The dome," Caleb whispered, cursing himself for not planning this better.

"I'll watch over everyone," Caduceus promised just as quietly and teasingly shooed him in the direction of the door.

Only when he made it into the hallway without waking anyone did Caleb feel a burst of nerves and excitement. Essek was here, waiting for him, and Caleb would not make either of them wait any longer. Caleb ensured none of the night watch was nearby when he reached the door for the captain's quarters and silently snuck inside. The drapes were still drawn from earlier but Caleb took the time to cast two simple spells: one to lock the door and one to stop noise from escaping the room.

"Always thinking ahead," Essek chuckled. The room was dark but brightened when Caleb opened the drapes of the stern-facing windows, allowing moonlight to pool on the floor and the bed where Essek sat. The Fjord-dummy had been moved to a corner of the floor.

Caleb noticed the jar of liquid Essek had brought and placed on the edge of the desk next to the bed. "I'm not the only one, I see."

Essek cleared his throat but offered a small smile. "I would rather not have anything else stop things tonight. I have wanted this for quite some time."

"As have I," Caleb assured him as he sat on the bed next to Essek. Their thighs were pressed tightly together and Caleb could feel Essek's heat through the fabric of their pants. He placed a palm on Essek's thigh and looked over at him. "You're sure?"

"I trust you so yes, I'm sure," Essek affirmed.

Essek leaned in first, hand on Caleb's cheek to turn his face into the kiss. It felt like they were two schoolboys experimenting for the first time and Caleb remembered that it was at least somewhat true. This was Essek's first time and it had been many years for Caleb. The angle was awkward with them sitting side by side but the innocence of it had Caleb melting into the weight of Essek's lips against his own. Caleb moved his hand from Essek's thigh to around his waist to keep him close and leaned more firmly into the kiss.

For a few minutes they remained like that, holding each other tightly as they kissed. Caleb took his time kissing Essek softly before nudging his lips apart to explore with his tongue. It felt so good to have Essek in his arms and kissing him back, and to know that for tonight they just had each other without any embarrassing questions or eavesdroppers. Caleb deepened the kiss as he caressed Essek's lower back and waist, swallowing Essek's moan at the increased touching.

Soon Caleb's veins were thrumming with arousal and he could tell Essek was in a similar state judging by the way he subtly arched his body into Caleb's touch. Caleb leaned away from the kiss and smiled when Essek tried to follow him, seeking more. Instead, Caleb gently pushed Essek backwards onto the mattress and straddled his abdomen. He focused on undoing the clasps of Essek's tunic, though Caleb's breathing turned shallow when Essek took the opportunity to explore Caleb's body with his hands. It was arousing having the Shadowhand's skilled, powerful fingers tasked with touching every inch of Caleb they could reach, especially when they pressed knowingly against Caleb's groin.

Caleb inhaled sharply and thrust into the heat and weight of Essek's hand. Caleb caught Essek's smirk in the beams of moonlight. "What are you smirking about?" Caleb asked even as he let his hips continue to sway into Essek's touch.

Essek's smirk softened into a smile. "You're normally so reserved. I enjoy having this effect on you."

Caleb studied Essek in the moonlight, relishing in the beauty of his body and soul. He was incredibly handsome with his piercing eyes, refined features and dark, warm skin. Essek was also unbelievably powerful, young for a drow and yet a master of his craft. To think that a lost Empire brat could meet and become entangled with a shy, highborn son of the Dynasty... There was so much stacked against them and yet here they were.

"I'm happy to have you here with me, Essek," Caleb confessed, voice brushing against the sensitive skin of Essek's ear. Caleb savoured the way Essek shivered beneath him and then got back to work on their clothes.

Essek sat up just long enough for Caleb to pull off his tunic when the clasps were undone, though the fabric was thrown haphazardly to the floor when Essek pulled Caleb back down into an impatient, heated kiss. Caleb flattened Essek against the mattress with his own body weight and locked their lips together, skimming his hands freely over any bared skin he could reach. While they kissed, Essek grasped the hem of Caleb's sleep shirt and tugged it upward until they finally had skin-to-skin contact.

Caleb yanked off his shirt before lying back down, their torsos pressed together. Caleb could feel the rise and fall of Essek's chest, and the stuttering of his breath when Caleb began kissing and sucking along the column of Essek's neck up towards his left ear. Caleb used his tongue to play with Essek's earring and then traced the shell of Essek's ear to the point and back down. Essek squirmed beneath him as Caleb devoted the same attention to Essek's right ear, bucking his hips up with a weak cry when Caleb bit down lightly on one earlobe.

"Sensitive," Caleb smirked.

"Tease," Essek retorted.

Caleb laughed and kissed the corner of Essek's mouth, not denying the accusation. "We don't have to go any further if you aren't ready."

"Don't you dare be chivalrous with me, Caleb Widogast," Essek narrowed his eyes. "I am neither fragile nor unwilling."

"Very well," Caleb conceded.

Without further protest, Caleb kissed from Essek's chin down his throat, chest and abdomen until he found Essek's belt. He watched Essek study his fingers as they unwound the belt and slid it free. The fastenings of Essek's pants were simpler and undone quickly but Caleb took his time inching them off Essek's hips and down his legs. Having teleported here directly, Essek had arrived shoeless and soon he was fully bared to the moon and Caleb's hungry gaze. Caleb took in every angle and curve, tasting every blemish and scar normally hidden by robes. He hoped to someday know the story behind each one, to know every inch of skin as sensitive as Essek's ears, but that would be for another time.

For now Caleb's focus was Essek's erection, which was swollen and curved up against his lower belly. Caleb had felt it throbbing against his own while he lay atop Essek but it was different to _see_ his effect on the drow. Caleb settled between Essek's legs and wrapped a fist around the base of Essek's cock, angling it upward. He then lapped his tongue against Essek's tip, pleased to already taste a hint of salt. Essek squirmed and cursed something in Undercommon but didn't tell Caleb to stop.

Their gazes locked as Caleb leaned forward. When he was certain Essek was paying attention and wouldn't look away, Caleb parted his lips and slowly took Essek into his mouth. The cursing in Undercommon got louder as Caleb cradled Essek's cock on his tongue, taking as much of his length as possible. It had been a long time but Caleb was determined to make Essek's first time memorable so he fought his gag reflex and sank down until his lips nearly met his fist.

"Caleb, _oh_..." Essek's lips parted as he moaned, eyes clenched closed with the pleasure. Essek reached down and tangled his fingers in Caleb's hair, not to pull Caleb off but simply to ground himself. "More, _please_ more."

Happy to oblige, Caleb hollowed his cheeks and sucked up Essek's cock back to the tip. He circled his tongue around the ridge of the head before opening his mouth to take him back in again. Caleb bobbed on Essek's length, sucking as much as he could while massaging the pulsing vein on the underside of Essek's cock with the pad of his thumb. Caleb had to use his free hand to pin Essek's hip to the bed, partly to keep him in place and partly to avoid gagging. Essek was thrusting up rhythmically now, following the movement of Caleb's mouth.

Essek began spilling precome onto Caleb's tongue, hinting that he was getting close even before Essek realized. Soon Essek was digging his heels into the mattress and tugging at Caleb's hair, trying to gently remove him. "Caleb, I'm close..." Caleb stubbornly remained where he was, moving his hand down from the base of Essek's cock to cradle and massage his balls. "Oh gods, stop! I want you inside me."

Caleb removed his mouth the instant Essek told him to stop, wanting to be certain Essek's only concern was finishing too soon. Essek was splayed on the bed, the moon highlighting his flushed skin and heaving chest. "I will not be done with you after one time," Caleb assured him, kissing one of Essek's inner thighs and then the other. "Finish for me now and then I will take you."

Essek exhaled heavily at the sensation of Caleb's lips circling him again. He didn't protest or plead further, merely watched Caleb work with his mouth and hand as his pleasure built. Caleb felt the way Essek's legs and abdomen tensed with the waves of arousal, each suck of his mouth nudging Essek closer to the edge. The end came between one breath and the next, Essek speaking Caleb's name like a hushed prayer before his back bowed and heat rushed into Caleb's mouth. He swallowed what he could and wiped away the remainder from his lips with the back of one hand.

When Caleb looked up he saw that all of the tension had left Essek's body. He was lying on the bed, eyes half lidded as he struggled to catch his breath. But Essek was still watching him, and smiled affectionately as Caleb moved closer. Caleb was uncertain how Essek would feel about tasting himself in Caleb's mouth, but Essek drew him into a deep, languid kiss without hesitation. Caleb kissed him back until Essek needed to lean away to breathe, his body still trembling with the aftershocks of his orgasm.

Caleb stood up briefly to remove his boots and pants, Essek watching him to ensure he stayed close. Then he lay down against Essek's side and grasped the jar of lubricant Essek had brought, twisting out the stopper. Caleb's erection ground against Essek's side, twitching at the heat of his body, but he planned to take the next part slowly. Caleb coated his longest finger in lubricant and reached down between Essek's legs, teasing the cleft of his ass and spreading lubricant. Since this was Essek's first time Caleb was certain this would be somewhat uncomfortable, but he hoped that preparing Essek while he was pliant in his post-orgasmic haze would make it easier.

Essek laid back against the pillow, relaxed and trusting. It was too soon for Essek to get hard again but the shallowness of his breathing demonstrated his arousal and enjoyment of Caleb's touching. Caleb coated his finger again and this time pressed the tip of his finger against Essek's ass, massaging the tight ring of muscles. Caleb's mouth moved back to Essek's pierced ear, offering a pleasant distraction when his finger finally breached Essek's body and pushed in. Essek tensed and inhaled sharply at the stretch while Caleb whispered soothing words into his ear.

Essek didn't ask Caleb to withdraw and so he didn't. Instead Caleb swirled his finger within Essek's body, further spreading lubricant and gently coaxing the muscles to relax and loosen. Caleb continued to kiss Essek's ear, his jaw, his throat, his chest, tasting every inch of Essek's body he could reach without disrupting the work of his finger. He noted when Essek's discomfort turned to pleasure and Caleb began slowly thrusting his finger in and out of Essek's body.

Caleb watched the way Essek's eyelashes fluttered with the pleasure and he smiled at Essek adoringly. "You are so incredibly beautiful." Essek scoffed. "Don't laugh," Caleb chided. "It's true. I've never—cared for anyone like I care for you," Caleb said, stumbling over the word he feared saying too soon. "You are very important to me."

Essek opened his eyes. His gaze was as warm as Caleb's was, his smile just as vulnerable. "You are very important to me as well. I care for you deeply."

Caleb's heart fluttered in his chest, overtaken by an emotion even more potent than arousal. He sealed their lips together, kissing Essek hard and relishing in the way Essek trembled with emotion as he kissed back. As they continued to kiss, Caleb curled his finger within Essek's body and smiled when Essek gasped into his mouth.

"Tease!" Essek accused when he recovered, his lips now swollen from kisses.

"Undeniably," Caleb agreed.

Caleb returned to thrusting his finger in and out of Essek's body, rutting against Essek's hip at the same time. Caleb was hard and eager to be inside Essek, already feeling how tight and hot he was. Essek adjusted his hips to offer a better angle for Caleb's finger and then reached down to grasp Caleb's cock in a fist. Each squeeze and stroke of Essek's hand on Caleb was curious and exploratory – and completely maddening. Caleb thrust up into Essek's grip, seeking more as he stretched Essek's entrance with his slicked finger.

Essek was a diligent study and quickly learned which movements of his hand made Caleb arch or moan, making it harder for Caleb to focus on the efforts of his own finger. Caleb removed his hand and coated two fingers in lubricant, knowing he could only last so long with Essek fisting his length. Essek's hand hesitated when he felt Caleb nudge two fingers against his ass, his attention momentarily diverted. He still didn't object though so Caleb slowly pushed the tips of both fingers in together. Caleb kept a close eye on Essek's face, reading the micro expressions of discomfort and then curiosity at the feeling of being stretched.

Caleb's fingers sank into Essek's body only as fast as Essek's body relaxed and allowed him in. It took a full minute but finally Essek was fully stretched around the width of Caleb's fingers. Essek groaned low and long and Caleb saw that Essek's cock was beginning to harden for a second time. As Caleb had suspected, Essek was young and sensitive enough to have a shortened refractory period. Essek began stroking Caleb anew but Caleb had to catch his wrist and stop him. "If you want me inside you, I can't last like that." Essek nodded and lifted Caleb's clean hand to kiss his fingertips. "How does it feel?"

"Odd, but no pain," Essek answered. "Better as I adjust."

After one final, lingering kiss, Caleb sat up and resituated himself between Essek's thighs, taking the bottle of lubricant with him. From this angle he could watch his fingers disappear into Essek's body and he felt a pulse of arousal for what would come next. Caleb stretched his fingers into a vee shape, loosening Essek's hole more aggressively now. Essek moaned and angled into it, showing no signs of pain.

"Are you ready?" Caleb wondered aloud as he stroked Essek's inner walls. "I could do three fingers to be safe."

"By the gods, Caleb!" Essek cursed. "If you don't fuck me right now, I'm leaving."

Caleb leaned over Essek's body enough for their eyes to lock. Then he shoved his fingers as deep into Essek's body as he could manage before curling them, brushing against Essek's prostate. The reaction was immediate. Essek threw his head back with a cry, his hands fisting the bed sheets below him. Caleb chuckled and massaged that gland with the pads of his two fingers, watching the way Essek arched and panted with pleasure. "That is such a lie."

"I want you—inside me when—I finish," Essek whispered between shaky breaths.

Caleb looked down and saw that Essek was indeed hard again, the head of his cock a darkened purple against the paler skin of his belly. Wanting to be inside Essek's body just as badly as Essek did, Caleb removed his fingers and sat back on his heels. "Hand me the pillow," he said, making a mental note to get a new pillow for the room at his next opportunity. Essek offered the pillow, lifting his body to assist as Caleb slid the pillow under his hips to improve the angle. "Now if it hurts—"

"Caleb!" Essek snapped.

" _Essek_ ," Caleb cut him off, his expression stern. "I'm not being difficult. We have all night and I don't want to hurt you unnecessarily so just tell me if it's too much, okay?"

Mollified, Essek nodded. "Alright."

Caleb reopened the jar and spread a liberal amount of lubricant over himself and between Essek's cheeks. Then he set the jar aside and shuffled as close to Essek's centre as he could get. With slippery fingers he led Essek's legs around him, Essek's knees hooking on his hipbones. Caleb took himself in hand, lining up the head of his cock against Essek's stretched entrance. Caleb leaned into it, using gravity rather than force to push against the resistance of Essek's body against the intrusion.

There were a few long seconds of stillness; neither of them moving, neither of them breathing. Between one heartbeat and the next, Essek relaxed and the head of Caleb's cock slipped into his body. Caleb froze there, catching Essek's wince of pain at the sudden stretch. He didn't withdraw though, instead distracting Essek through the moment of pain by stroking his flagging erection with a hand. With slow, shallow thrusts Caleb pushed himself deeper, feeling the way Essek's cock twitched and swelled in his hand with each careful thrust.

Finally Caleb was fully seated with his balls against Essek's ass and the entire length of his cock filling his body. Essek's cock was fully hard again and his look of pain was gone, replaced by a dazed pleasure as he panted through parted lips. "So beautiful," Caleb repeated quietly, fearful of breaking the spell that was this moment shared between them. Essek seemed beyond words at the moment but he met Caleb's gaze through his lashes and offered a warm smile.

Caleb pulled out until only the head of his cock was spreading Essek open and then he thrust back in, smooth and firm. Essek didn't wince, only groaned and arched into it. Caleb repeated the movement, harder, and then harder again until Essek's entire body shuddered against the mattress with the impact of Caleb's thrusts inside him. Essek had adjusted to Caleb's girth but he was still tight and incredibly hot, squeezing Caleb's length each time he drew out and thrust back in.

The temperature in the small room seemed to rise, both of them sweaty and short of breath. Neither of them stopped though, Caleb rutting forward at a steady rhythm now and Essek clenching around him. Caleb placed both hands on Essek's hips and shifted him slightly on the pillow, trying different angles of his hips with each forward motion until he found Essek's prostate again. Essek gasped and bucked into it, his lower back leaving the mattress entirely.

Caleb felt the fire inside him building, his body tense and desperate with heat pooling at the base of his spine. He used his hands to hold Essek down, grinding against that sensitive gland and forcing Essek to take every second of pleasure. Caleb could see that Essek was beginning to spill precome on himself, another little dribble escaping with every thrust against his prostate. Essek was completely pliant under Caleb, trembling and trusting Caleb to give them both the pleasure they needed.

Caleb never wanted this to end; he never wanted their bodies to separate from their intimate connection or to have Essek out of his sight again. But his arousal was a wildfire now, untameable and out of control. Caleb could feel the coil of heat in his gut tightening, warning of his approaching end. He could tell Essek was the same, his whole body flushed and his cock thick and hard. There was no holding off now unless Caleb fully withdrew from Essek's body, which he was unwilling to do, so Caleb gave himself permission to race them both over the edge.

After ensuring that he still had the right angle to nudge the head of his cock against Essek's prostate with each thrust, Caleb wrapped one hand around Essek's length. Caleb stroked him firmly in time with each of his thrusts, memorizing each pleasured noise that escaped Essek's lips. Caleb's hand was sticky with Essek's precome now and his hips had lost their rhythm, his cock spearing into Essek's body with animalistic need.

"I can't hold off," Essek groaned.

Caleb rubbed the pad of his thumb over Essek's tip in a swirling motion. "You're not supposed to."

Essek started to laugh, a light and innocent sound that was quickly cut off by a curse and a plea. Caleb fulfilled that plea by fucking into Essek as deep as he could, stroking Essek's length as tightly as he dared. It took three more thrusts from Caleb before Essek's entire body stiffened, a drawn out moan escaping Essek as his come spilled across himself and pooled in his belly button.

Caleb fucked him through it, jerking Essek's cock until his hand was batted away due to oversensitivity. Then he took a bruising grip on Essek's hips, rocking into Essek's tight heat. Caleb was so close, his cock being milked by each squeeze and release of Essek's ass around him as Essek worked through his orgasm.

"Fill me," Essek murmured, and that was all Caleb needed.

One, two more frantic thrusts and Caleb froze as the flames of pleasure that had been building combusted in a burst and consumed him. His hips twitched with each spasm of his climax, shooting thick ropes of come deep within Essek's body. Even when Caleb was finished spilling his seed he didn't move, his eyes closed and his mind fuzzy. It was Essek's touch on his forearm that brought Caleb back from oblivion and he carefully eased his softening cock out of Essek.

On shaky limbs Caleb moved to grab his shirt to wipe them off but Essek held Caleb's wrist in his grasp and pulled him closer instead. Caleb lay down curled up against Essek's side with a satiated sigh, resting his head on Essek's chest to hear his hurried heartbeats slow. Essek wrapped one arm around Caleb's shoulders to keep him close and used his other hand to lift Caleb's forearm, kissing along the scars marring his skin.

"I don't want to be apart from you," Caleb confessed weakly after a few minutes of comfortable silence. He knew things weren't that simple but he wanted Essek to hear the words all the same, to know that this was about more than just sex.

Essek kissed his forehead. "Perhaps someday we can accomplish that. But we have our roles, and your friends will need time."

Caleb sighed, feeling foolish for his sentimentality when Essek was speaking so logically. "I know."

The words came out harsher than he meant and Essek was nothing if not perceptive. Caleb was rolled onto his back and Essek climbed on top of him, pressing their foreheads together. "You have asked me, twice now, to find my better self. But I have already found him, every time I am in your presence." Essek kissed Caleb softly, sweetly, and then continued. "We are the same so I know you fear the loss that can follow attachment the way I do. But I plan to love you fiercely for all of my remaining days."

Caleb knew Essek cared for him but there was something powerful about that one word being spoken aloud. Caleb was even more stunned to hear Essek say it first, reserved as he normally was. Essek had been right; Caleb _was_ scared. But of all the risks Caleb had taken in his life, loving Essek had to be the easiest. "You are mine," Caleb stated with certainty. "And I will love you forever, on any plane of existence."

"Good," Essek smiled, and they sealed it with a kiss.

**Author's Note:**

> Find me on: [Tumblr](http://onewhositswiththeturtles.tumblr.com/) and [Pillowfort](https://www.pillowfort.io/onewhositswiththeturtles).


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